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Freddie Prinze Jr. Zach Siler Rachael Leigh Cook Laney Boggs Paul Walker Dean Sampson Jodi Lyn O'Keefe Taylor Vaughan Kevin Pollak Wayne Boggs Anna Paquin Mackenzie Siler Kieran Culkin Simon Boggs Elden Henson Jesse Jackson Matthew Lillard Brock Hudson Usher Campus D.J. Lil' Kim Alex Gabrielle Union Katie Dulé Hill Preston Tamara Mello Chandler Clea DuVall Misty Tim Matheson Harlan Siler Debbi Morgan Ms. Rousseau Alexis Arquette Mitch Dave Buzzotta Jeffrey Munge Rylander Chris Owen Derek Funkhouser Rutley Charlie Dell Man in Falafel Barn Michael Milhoan Principal Stickley Carlos Jacott Prom Photographer Ashlee Levitch Melissa Vanessa Lee Chester Girl #2 Patricia Charbonneau Lois Siler Katharine Towne Savannah Wendy Fowler Harmony Flex Alexander Kadeem Robert Baglia Beatnik Debbie Lee Carrington Felicity Sara Rivas Vampire Girl Clay Rivers Gustave Amon Bourne 'She's All That' Rapper Takbir Bashir 'She's All That' Rapper Anthony 'Click' Rivera 'She's All That' Rapper Jarrett Lennon Naylon Brandon Mychal Smith JV Cleaning Boy Milo Ventimiglia Soccer Player Kente Scott Sophomore Boy Kim Cottom Dancer T.J. Espinoza Dancer Brian Friedman Dancer Tony Fugate Dancer Caroline Girvin Dancer Alicia Gilley Dancer Scott Hislop Dancer Jennifer Lee Keyes Dancer Richard Kim Dancer Stephanie Landwehr Dancer Dani Lee Dancer Joe Loera Dancer Mayah McCoy Dancer Ayesha Orange Dancer Robert Schultz Dancer Josh Seffinger Dancer Sarah Christine Smith Dancer Christopher Smith Dancer Bree Turner Dancer Christine Vincent Dancer Jerry 'Flo Master' Randolph Dancer Sarah Michelle Gellar Cafeteria Girl